Seed Fatty Acid Compositions and Chemotaxonomy of Wild Crambe (Brassicaceae) Taxa in Turkey

Home , Crambe

Turkish Journal of Agriculture and Forestry Turk J Agric For (2020) 44: 662-670 http://journals.tubitak.gov.tr/agriculture/ © TÜBİTAK Research Article doi:10.3906/tar-1912-76

Seed fatty acid compositions and chemotaxonomy of wild Crambe (Brassicaceae) taxa in Turkey

İlhan SUBAŞI* Central Research Institute for Field Crops, Ankara, Turkey

Received: 31.12.2019 Accepted/Published Online: 01.09.2020 Final Version: 08.12.2020

Abstract: Wild Crambe species have greater potential than Crambe hispanica in industry, medicine, as a vegetable, etc. A total of 53 germplasm accessions, belonging to 7 taxa, were collected from the natural flora of Turkey. The accessions consisted ofC. orientalis var. orientalis (18 accessions), C. orientalis var. dasycarpa (1 accession), C. orientalis var. sulphurea (2 accessions), C.tataria var. aspera (3 accessions), C. tataria var. tataria (26 accessions), C. grandiflora (1 accession), C. orientalis var. sulphurea, and C. maritima (2 accessions). In this study, the seed fatty acid compositions and oil contents were determined, and the data were used for taxonomic cluster, correlation, and principal component analyses. Important correlations were determined among the fatty acids; however, the oil contents were not correlated. Altitude was positively correlated with linolenic acid, while negatively correlated with oleic and linoleic acid. For the principal component and correlation analyses, 7 major fatty acids (>1%) were used, including palmitic (C16:0), oleic (C18:1), linoleic (C18:2), cis-11 eicosenoic (20:1), linolenic (C18:3), erucic (C22:1), and nervonic acid (C24:1). A total of 17 fatty acids were used for the cluster analyses. Two major clusters were formed, where the first consisted of C. orientalis, C. tataria, and C. grandiflora taxa, while the second consisted of only C. maritima taxa. The dendrogram based on the fatty acid values clearly discriminated the species groups; however, C. tataria was not located close to C. maritima, contrary to previous molecular cluster studies.

Key words: Chemotaxonomy, fatty acid composition, seed oil content, wild Crambe

1. Introduction The oil content of cultivated C. abyssinica species Indigenous plants form the bedrock of diversity in has been reported to have a wide range of variation, industrial systems. Deficiently used industrial crop from 24% to 46% (Warwick and Black, 1997; Gastaldi et genetic resources have great potential as an alternative to al., 1998; Comlekcioglu et al., 2008; Rudloff and Wang, worldwide known species or varieties that are commonly 2011; Uyaroğlu, 2018). The total fatty acid composition produced and consumed. With climate uncertainty, there comprised 53.9%–63.1% erucic acid (Vollmann and is an urgent need to diversify plant resources to a wider Ruckenbauer, 1993). Little information on the oil content range of crops for greater system resistance (Zia-Ul-Haq et of other wild Crambe species has been reported. The al., 2013; Colak et al., 2019). whole-seed oil content was reported as 11% and 15% in The genus Crambe comprises annual, biennial, and C. orientalis and C. tataria, respectively (Comlekcioglu perennial species (Comlekcioglu et al., 2008). It has et al., 2008). However, although the reported oil and potential in terms of use in the oleochemical industry; erucic acid rates of wild Crambe species have been low, however, currently, C. abyssinica Hochst. is the only they are a significant source of genetic variation for fatty species of Crambe that is used in industry (Warwick and acid composition. Wild Crambe seed oil mainly contains Black, 1997). Due to its high amount of erucic acid, which palmitic, oleic, cis-11 eicosenoic, erucic, linoleic, and provides high boiling and evaporating points, it is widely linolenic acid. used in industrial applications, such as the production of Understanding the genetic potential and characteristics plastic film, nylon, coatings, and lubricants (Warwick and of wild relatives of the different plant species is important Black, 1997; Piovan et al., 2011). for long-term breeding programs (Ersoy et al., 2018; There are 6 species and 4 intraspecific taxa in the Gecer et al., 2020). In addition, many wild species have natural flora of Turkey, while there are 35 taxa worldwide the potential to become new valuable crop plants. As (Prina, 2009; Mutlu, 2012; Bassegio et al., 2016; Tarıkahya- an industrial oil source, wild relatives of Crambe may Hacıoğlu, 2016). possess many important agronomical properties, such * Correspondence: [email protected] 662

This work is licensed under a Creative Commons Attribution 4.0 International License. SUBAŞI / Turk J Agric For as cytoplasmic and nuclear male infertility, disease and were set at 250 °C. The column was programmed with the pest resistance, C3-C4 photosynthetic activity, and cold, following temperature regime: hold at 140 °C for 5 min, drought, and salinity resistance; therefore, they could be ramp to 240 °C at 4 °C/min, and hold at 240 °C for 20 used in breeding programs (Warwick et al., 2009). min. Fatty acid methyl esters (FAMEs) were identified In this study, it was aimed to determine the seed oil by comparison of their retention times with those of the properties of some wild Crambe accessions and investigate reference standards (Restek FAME Mix 37). The fatty acid whether the seed oil compositions could be used as a content was calculated based on the peak area ratio and taxonomical character for different Crambe species and expressed as grams of fatty acid/100 g of oil. taxa. 2.3. Statistical analysis All statistical analyses were performed using JMP Pro 11 2. Materials and methods (SAS Institute Inc., Cary, NC, USA, 2013). Correlation 2.1. Material among the studied traits was calculated using the Pearson Crambe seeds were obtained from multiple flora collection correlation procedure implemented in the mentioned expeditions in 2014 in Turkey. Among these, 53 germplasm statistical program. Principal component analysis (PCA) accessions were chosen to represent 7 Crambe taxa was performed using the fatty acid (palmitic, oleic, linoleic, collected from different regions of Turkey, comprising18 of linolenic, cis-11 eicosenoic, and erucic acids) values of C. orientalis var. orientalis, 1 of C. orientalis var. dasycarpa, each of the 7 accessions. For chemotaxonomic evaluation 2 of C.orientalis var. sulphurea, 3 of C. tataria var. aspera, of the 7 Crambe taxa, the mean values of the 17 fatty acids 1 of C. grandiflora, 21 of C. tataria var. tataria, and 2 of C. were used to perform the cluster analyses. maritima. Each taxon is listed in Table 1. The distribution of the species in Turkey is given in Figure 1.C. orientalis 3. Results was collected at an altitude of 800–1897 m, C. tataria at Within the wild relative species of Crambe, 17 fatty acids 744–1347 m, and C. maritima at 0–4 m. were determined, of which the 7 main fatty acids (>1%) were palmitic (C16:0), oleic (C18:1), linoleic (C18:2), cis- 2.2. Extraction and gas chromatography 11 eicosenoic (20:1), linolenic (C18:3), erucic (C22:1), and The oil contents and compositions were determined in nervonic (C24:1) (Table 2). Acids identified with <1% of the the laboratories of the Central Research Institute for total fatty acid content were myristic (C14:0), palmitoleic Field Crops of the Ministry of Agriculture and Forestry, (C16:1), stearic (C18:0), arashidic (C20:0), heneicosanoic in Ankara, Turkey. Determination of the oil contents was (C21:0), cis-11,14-eicosadienoic (C20:2), behenic (C22:0), performed following the method of Matthäus and Brühl cis-11,14-eicosadienoic (C20:2), cis-13,16-docosadienoic (2001), with some modifications. First, 5 grams of whole (C22:2), and lignoceric (C24:0) (Table 3). seeds were milled in a Foss KN 195 Knifetec laboratory The maximum and minimum oil contents for palmitic mill (Hillerød, Denmark). Afterwards, the extraction was (C16:0), oleic (C18:1), linoleic (C18:2), cis-11 eicosenoic performed for 3 h using a Soxhlet extractor (Soxtherm 2000 (C20:1), linolenic (C18:3), erucic (C22:1), and nervonic automatic, C. Gerhardt GmbH & Co. KG, Königswinter, (C24:1) acid were determined as 4.70%–20.50%, 0.17%– Germany) with hexane. After extraction, the solvent was 5.78%, 15.02%–32.49%, 3.94%–17.45%, 10.76%–21.79%, evaporated at 103 °C for 2.5 h, cooled for 30 min in a 2.18%–9.57%, 22.59%–49.68%, and 0.79%–2.86% in desiccator, and weighed. The seed oil content was reported all of the Crambe accessions, respectively (Table 2). C. as the mass percent [crude oil weight (g)/ground seeds orientalis accessions were identified as possessing higher weight (g) × 100]. mean values of erucic acid than the other Crambe species For determination of the fatty acid compositions, the accessions. method given by Sampaio et al. (2012) was followed, with According to the biplot diagram, 71% of the total some modifications. First, 0.1 g of oil was dissolved in 10 mL variation was explained (Figure 2). The first 4 eigenvalues of n-hexane, to which 0.5 mL of 2 N potassium hydroxide/ were 3.57, 1.47, 0.72, and 0.59. For taxonomic evaluation, methanol solution was added, and then incubated for 30 the mean values of all of the determined seed fatty acids min at room temperature. The fatty acids were esterified were used. As in the cluster analyses, all accessions as methyl esters and placed into a Shimadzu AOC-20i belonging to the same species revealed close associations. automatic injector (Shimadzu Corp., Kyoto, Japan) (split There were 4 species groups, comprisingC. orientalis, C. ratio 1:100). The methyl ester phase was analyzed using a grandiflora, C. tataria, and C. maritima. C. grandiflora was Shimadzu GC-2010 system equipped with a Teknokroma located in the C. orientalis accession group, while the C. capillary column (Teknokroma Anlítica, SA, Barcelona, maritima accessions were placed close to the C. tataria Spain) (100 m × 0.25 mm and 0.2 µm) and flame ionization group. detector. Helium was used as the carrier gas at a flow rate Table 4 shows the major fatty acid compositions (>1%) of 0.94 mL/min. The injector and detector temperatures of all of the germplasm accessions. The total variation and

663 SUBAŞI / Turk J Agric For

Table 1. List of investigated Crambe germplasm accessions and localities.

Accession Accession Taxon No Locality. Altitude Taxon No. Locality Altitude code code C. orientalis var. 1 1C.o_o Ankara 800 C. tataria var. tataria 28 28C.t_t Kırıkkale 892 orientalis 2 2C.o_o Malatya 918 29 29C.t_t Eskişehir 895 3 3C.o_o Malatya 924 30 30C.t_t Afyon 903 4 4C.o_o Nevşehir 935 31 31C.t_t Eskişehir 940 5 5C.o_o K.Maraş 943 32 32C.t_t Ankara 950 6 6C.o_o Nevşehir 964 33 33C.t_t Ankara 950 7 7C.o_o Aksaray 976 34 34C.t_t Aksaray 970 8 8C.o_o Elbistan 1050 35 35C.t_t Ankara 1000 9 9C.o_o Elazığ 1118 36 36C.t_t Eskişehir 1009 10 10C.o_o Elbistan 1143 37 37C.t_t Elbistan 1039 11 11C.o_o Kayseri 1191 38 38C.t_t Ankara 1078 12 12C.o_o Adıyaman 1222 39 39C.t_t Kırşehir 1080 13 13C.o_o Kayseri 1400 40 40C.t_t Kırşehir 1096 14 14C.o_o Erzincan 1431 41 41C.t_t Afyon 1115 15 15C.o_o Kars 1677 42 42C.t_t Kırşehir 1150 16 16C.o_o Van 1725 43 43C.t_t Kırşehir 1138 17 17C.o_o Kars 1793 44 44C.t_t Kayseri 1162 18 18C.o_o Erzurum 1897 45 45C.t_t Kayseri 1197 C. orientalis var. 19 19C.o_d Adana 1076 46 46C.t_t Kırşehir 1200 dasycarpa C. tataria var. 20 20C.t_a Ankara 1059 47 47C.t_t Afyon 1249 aspera

21 21C.t_a Ankara 1127 48 48C.t_t Nevşehir 1347

22 22C.t_a Ankara 1135 C. grandiflora 49 49C.g Şanlıurfa 777

C. tataria var. 23 23C.t_t Ankara 744 C. maritima 50 50C.m Sinop 0 tataria 24 24C.t_t Ankara 791 51 51C.m Kastamonu 4 C. orientalis var. 25 25C.t_t Eskişehir 855 52 52C.o_s K.Maraş 1456 sulphurea 26 26C.t_t Bilecik 878 53 53C.o_s K.Maraş 1122 27 27C.t_t Kırıkkale 892 mean of each major fatty acid in the genus Crambe were Intraspecific fatty acid variations of the C. tataria compared to the intraspecies averages and variations of species (coefficient of variation (CV) C.t) were lower than the fatty acids of the C. orientalis and C. tataria species those of all of the other Crambe accessions (total CV) and (Figure 3). those of the C. orientalis accessions (CV C.o). This showed The highest variations were observed in palmitic (16:0), that the fatty acids in C. tataria were more stable than linolenic (18:3), linoleic (18:2), and nervonic (24:1) acid, those of the other Crambe species. respectively, while the lowest variations were observed Despite having different climatic and environmental in cis-11-eicosenoic (20:1), erucic (22:1), and oleic (18:1) factors, the Crambe species collected from different acid. locations in the natural flora exhibitedintraspecific

664 SUBAŞI / Turk J Agric For

Figure 1. Distribution map of the investigated Crambe species. genotypic stability in terms of their fatty acids. In this content in C. orientalis and C. tataria was reported as 45% respect, cis-11-eicosenoic, erucic, and oleic acid, which and 25%, respectively (Lazzeri et al., 1994; Comlekcioglu had relatively lower variations in the genus Crambe, played et al., 2008). a more decisive role in the species separations. In previous studies conducted on C. orientalis, C. Correlations between the altitude, oil ratio, and 7 tataria, and C. maritima, the main fatty acid contents were major fatty acid values were investigated. There was a determined as follows: erucic: 34.69%–39.39%, 27.0%– positive correlation between altitude and linolenic acid 29.87%, and 21.60%–32.60%; cis-11-eicosenoic: 11.34%– and a negative correlation between altitude and the oleic 20.00%, 7.70%–21.00%, and 14.50%–18.50%; linolenic: and linoleic acid contents. 7.55%–21.21, 11.00%–15.01%, and 4.80%–8.60%; linoleic: A high positive correlation was found among the oleic, 9.76%–13.07%, 9.00%–15.00%, and 21.2%–25.3%; oleic: linoleic, and cis-11-eicosenoic acid contents. However, 1.61%–25.05%, 14.00%–21.00%, and 18.80%–26.70%; and this group was negatively correlated with the palmitic palmitic: 2.00%–3.27%, 2.00%–2.3%, and 1.80%–4.10% and erucic acid contents. A negative correlation was also (Miller et al., 1965; Dolya et al., 1973; Goffman et al., 1999; found between linolenic acid and the oleic and nervonic Comlekcioglu et al., 2008). fatty acid contents (Table 4 and Figure 2). The possible In the current study, the erucic acid content was higher positive correlation between linoleic and linolenic acid can in C. tataria and C. maritima when compared to previous be explained by the synthesis pathway of these fatty acids reports, and was consistent with that of C. orientalis. (Saastamoinen et al., 1989). However, the findings for linoleic acid were lower in C. orientalis and C. maritima. Moreover, the oleic acid 4. Discussion content was slightly higher and that of linolenic acid was Cultivated Crambe (Crambe abyssinica Hochst.) comprises lower than that mentioned in studies of C. orientalis and C. industrial properties because its oil (30%–45% of the seed tataria. The palmitic acid content was similar to that of all weight) has a high content (55%–62.5%) of erucic acid reported studies on all of the investigated Crambe species. (Wang et al., 1995, Lalas et al., 2012, Tarıkahya-Hacıoğlu, C. Orientalis var. orientalis, accession 12 (12Co_o) (listed 2016). C. hispanica is quite similar to C. abyssinica in Table 1), had the highest erucic acid rate (49.68%) (Mikolajczak et al., 1961), which has been grown among the accessions, while C. orientalis var. orientalis, successfully (Miller et al., 1965). According to the current accession 9 (9Co_o), had the highest oil content (20.50%). results, the oil content of the wild Crambe species was As in many plant families, the family Brassica has lower (4.7%–20.5%) than that of the cultivated Crambe. a large number of wild relatives and can be used for The difference in the oil contents between the whole and breeding. However, in long-term breeding programs, dehulled seeds was 11%, 15%, and 8.5% in C. orientalis, the superior characteristics and phylogenic relationships C. tataria, and C. abyssinica, respectively. The pericarp among these wild relatives can also be used. Although

665 SUBAŞI / Turk J Agric For

Table 2. Oil and major fatty acid contents of the investigated Crambe taxa (%).

Accession code Oil rate C16:0 C18:1 C18:2 C20:1 C18:3 C22:1 C24:1 1C.o_o 9.20 2.51 20.45 10.56 16.10 7.95 37.57 1.23 2C.o_o 6.81 4.65 23.66 3.94 15.28 2.18 41.96 2.86 3C.o_o 4.84 5.78 18.57 5.75 14.65 3.84 43.25 1.30 4C.o_o 11.30 2.87 21.05 11.24 16.74 7.98 35.41 1.17 5C.o_o 4.70 0.41 17.17 4.13 14.55 2.87 47.66 1.29 6C.o_o 12.20 2.78 23.94 10.63 18.23 7.00 33.31 1.11 7C.o_o 7.90 2.92 22.24 11.05 16.93 7.63 34.16 1.41 8C.o_o 13.90 2.66 15.16 10.40 12.81 8.61 45.49 1.48 9C.o_o 20.50 3.08 15.02 10.59 12.66 8.91 44.25 1.41 10C.o_o 7.62 3.12 17.94 7.70 13.95 5.02 46.64 1.47 11C.o_o 14.20 2.53 19.38 8.07 17.30 6.84 41.14 1.40 12C.o_o 8.87 3.65 16.60 8.05 10.76 4.14 49.68 2.28 13C.o_o 9.80 2.53 23.89 9.83 17.65 8.08 33.79 1.03 14C.o_o 12.00 3.23 23.34 11.12 17.51 7.50 31.83 1.61 15C.o_o 10.44 2.72 25.11 11.21 14.88 8.42 33.14 1.36 16C.o_o 7.71 2.68 17.64 11.68 15.16 9.09 38.21 1.51 17C.o_o 10.42 2.33 21.27 11.45 17.03 9.57 33.83 1.32 18C.o_o 12.54 2.77 24.94 10.66 17.34 8.15 31.50 1.46 19C.o_d 9.60 2.79 25.05 9.63 17.48 7.55 32.95 1.03 20C.t_a 10.50 2.64 24.84 11.34 21.20 4.06 30.52 1.54 21C.t_a 9.20 2.01 27.04 13.03 19.73 6.95 26.87 1.15 22C.t_a 7.60 2.20 25.06 12.64 17.31 4.55 32.77 1.60 23C.t_t 10.70 1.85 19.34 13.82 18.05 9.15 32.90 1.37 24C.t_t 10.50 2.08 22.62 12.89 18.53 6.28 32.81 1.53 25C.t_t 8.70 2.47 24.15 13.71 19.01 4.55 30.50 1.63 26C.t_t 8.80 2.23 26.32 10.36 20.38 4.85 31.33 1.24 27C.t_t 6.60 2.21 24.68 13.89 18.80 6.79 28.57 1.25 28C.t_t 7.00 2.18 28.56 9.91 21.04 4.24 29.53 1.40 29C.t_t 10.40 1.79 20.14 15.48 17.83 9.22 31.05 1.36 30C.t_t 12.40 2.03 27.82 11.41 21.74 5.82 27.55 1.05 31C.t_t 8.70 2.18 23.09 13.03 19.94 5.73 31.07 1.33 32C.t_t 10.50 2.17 24.92 13.63 20.17 6.38 28.47 1.17 33C.t_t 8.58 0.21 28.13 9.48 20.74 3.39 30.59 1.32 34C.t_t 11.40 1.98 26.00 9.93 21.35 7.96 28.49 1.06 35C.t_t 11.50 1.90 18.46 14.21 17.51 8.32 34.36 1.51 36C.t_t 7.00 2.37 21.71 16.24 17.68 7.56 29.14 1.28 37C.t_t 12.40 2.32 25.62 10.59 20.97 5.53 30.48 1.26 38C.t_t 9.50 2.54 25.28 12.66 20.00 5.37 29.27 1.37

666 SUBAŞI / Turk J Agric For

Table 2. (Continued).

39C.t_t 9.70 2.19 25.8 13.67 20.28 6.95 26.84 1.09 40C.t_t 7.60 2.24 24.56 13.47 19.04 7.70 28.27 1.23 41C.t_t 5.10 2.37 21.71 14.59 17.22 8.02 30.66 1.38 42C.t_t 11.60 1.86 23.11 11.09 19.86 8.52 30.89 1.33 43C.t_t 9.26 0.17 25.09 13.29 20.39 7.12 27.41 1.43 44C.t_t 9.10 2.23 23.21 15.39 18.88 7.56 28.25 1.21 45C.t_t 11.20 2.01 25.33 12.96 19.42 7.08 28.67 1.21 46C.t_t 8.00 2.42 20.95 12.69 18.95 6.24 33.37 1.62 47C.t_t 9.60 2.37 24.39 14.11 18.28 7.50 28.87 1.21 48C.t_t 9.50 2.02 22.78 11.16 21.79 6.93 30.69 1.35 49C.g 7.40 3.07 17.13 10.68 11.26 7.65 30.89 1.96 50C.m 14.05 1.81 31.30 17.34 17.14 3.37 25.17 1.27 51C.m 12.63 1.84 32.49 17.45 17.26 3.32 22.59 0.79 52C.o_s 13.74 2.59 22.63 11.42 18.70 5.20 32.32 1.81 53C.o_s 10.58 2.96 23.81 8.10 18.15 4.04 37.76 1.68 x̄ (total) 9.92 2.41 23.03 11.57 17.84 6.51 33.11 1.39 x̄ (C.o) 10.24 2.95 20.65 9.35 15.63 6.91 38.72 1.46 x̄ (C.t) 9.4 2.04 24.16 12.78 19.52 6.56 30.01 1.33 CV (total) 27.5 35.83 16.23 24.24 14.47 29.02 17.97 22.9 CV (C.o) 35.79 35.03 16.58 25.97 13.05 31.77 15.53 29.69 CV (C.t) 19.01 27.12 10.41 13.72 6.99 23.52 6.63 12.15

Table 3. Mean values of the oil and fatty acid contents of the 7 Crambe taxa (%).

Taxon Oil rate (%) Oil rate acid (C14:0) Myristic acid (C16:0) Palmitic acid (C16:1) Palmitoleic acid (C18:0) Stearic acid (C18:1) Oleic acid (C18:2) Linoleic acid (C20:0) Araşidic acid (20:1) Cis-11-eicosenoic acid (C18:3) Linolenic acid (C21:0) Heneicosanoic acid C20:2 Cis-11,14-eicosadienoic Behenic acid (C22:0) Erusic acid (C22:1) acid (C20:2) Cis-11,14-eicosadienoic acid (C22:2) Cis-13,16-docosadienoic Lignoseric acid (C24:0) acid (C24:1) Nervonic

C. grandiflora 7.43 0.14 3.07 0.26 0.66 17.13 10.68 1.49 11.26 7.65 0.55 0.39 0.89 42.97 0.42 0.20 0.00 1.96 C. maritima 13.34 0.00 1.83 0.00 0.59 31.90 17.40 0.35 17.20 3.35 0.64 0.76 0.19 23.88 0.00 0.18 0.00 1.03 C. orientalis_dasycarpa 9.65 0.00 2.79 0.19 0.84 25.05 9.63 0.54 17.48 7.55 0.22 0.50 0.37 32.95 0.49 0.22 0.15 1.03 C. orientalis_orientalis 11.24 0.07 3.09 0.23 0.80 21.74 9.38 0.49 15.98 6.69 0.15 0.57 0.38 37.85 0.60 0.30 0.12 1.46 C. orientalis_sulphurea 12.16 0.10 2.78 0.19 0.92 23.22 9.76 0.92 18.43 4.62 0.44 0.52 0.39 35.04 0.29 0.26 0.19 1.75 C. tataria_aspera 9.63 0.08 2.42 0.20 0.70 24.14 11.98 0.36 18.61 5.62 0.44 0.64 0.26 32.23 0.55 0.25 0.11 1.38 C. tataria_tataria 9.61 0.08 2.20 0.18 0.69 23.82 12.44 0.36 19.44 6.50 0.41 0.69 0.25 30.78 0.45 0.23 0.10 1.33

667 SUBAŞI / Turk J Agric For

Figure 2. 2D PCA of the major fatty acid data of the 7 Crambe taxa with 53 accessions.

Table 4. Coefficients of correlation between the oil and major fatty acid contents of the 53Crambe accessions (%).

Altitude Oil rate C16:0 C18:1 C18:2 C20:1 C18:3 C22:1 C24:1 Altitude 1 Oil rate –0.01 1 C16:0 0.146 –0.059 1 C18:1 –0.312* 0.026 –0.321* 1 C18:2 –0.274* 0.172 –0.393** 0.368** 1 C20:1 –0.055 0.004 -0.47** 0.683** 0.333* 1 C18:3 0.442** 0.263 –0.075 –0.358** 0.322* –0.077 1 C22:1 0.227 –0.034 0.435** –0.779** –0.737** –0.722** –0.105 1 C24:1 0.164 –0.162 0.421** –0.369** –0.416** –0.427** –0.298* 0.465** 1

*P < 0.05, **P < 0.01. molecular phylogenetic relationships among the taxa have separate branch than all of the other taxa. C. grandiflora and been investigated, no chemotaxonomic studies have been C. orientalis taxa formed a cluster together. conducted on their fatty acids. In the species belonging to Crambe and other Brassicaceae family members, fatty 5. Conclusion acids, and especially, the erusic acid content, are important Crambe is a plant that may have significant potential in the in chemotaxonomic classification (Appelqvist, 1971; future with regards to use in industry, medicine, and as Umarov, 1975). In this study, it was investigated whether vegetable. For breeding programs, genotypes that have a fatty acids can be a chemotaxonomic criterion. According wide variation are required. Determination of the genetic to the dendrogram (Figure 4), based on the fatty acid affinities among the taxa is facilitative for breeders. This compositions, C. maritima was separated from all of the study showed the Crambe species in Turkey were divided other taxa and later, C. grandiflora was located on a separate into 2 major groups, with C. maritima in the first and the branch than C. orientalis and C. tataria. In the subbranches, other Crambe species in the second . C. orientalis taxa were clustered together and C. tataria taxa Herein, it was seen that the seed fatty acids supported were clustered together. When compared with the molecular the current taxonomic classification. Hence, seed fatty acids analyses of previous studies (Tarıkahya-Hacıoğlu, 2016), it can be used as a taxonomic character and can distinguish was seen that C. maritima and C. tataria were located on a Crambe taxa at the species and subspecies level.

668 SUBAŞI / Turk J Agric For

Figure 3. Means and CV of the oil ratio and major fatty acid values of C. orientalis, C. tataria, and all of the other Crambe accessions.

Figure 4. Dendrogram created with mean values of the 17 fatty acids of the wild Crambe taxa.

Acknowledgments would like to thank Yusuf Arslan and Burcu Tarıkahya- This research was financed by the General Directorate Hacıoğlu for their continuous and generous support, of Agricultural Research and Policy (Republic of Turkey and for accompanying the author on the collection Ministry of Agriculture and Forestry). The author expeditions.

669 SUBAŞI / Turk J Agric For

References

Appelqvist LA (1971). Lipids in Cruciferae: VIII. The fatty acid Miller RW, Earle FR, Wolff IA, Jones Q (1965). Search for new composition of seeds of some wild or partially domesticated industrial oils. XIII. Oils from 102 species of Cruciferae. species. Journal of the American Oil Chemists’ Society 48 (11): Journal of the American Oil Chemists’ Society 42: 817-821. 740-744. doi: 10.1007/BF02541165 Bassegio D, Zanotto MD, Santos RF, Werncke I, Dias PP (2016). Mutlu B (2012). Crambe. In: Güner A, Aslan S, Ekim T, Vural M, Oilseed crop crambe as a source of renewable energy in Brazil. Babac MT (editors). Türkiye Bitkileri Listesi (Damarlı Bitkiler). Renewable and Sustainable Energy Reviews 66: 311-321. doi: İstanbul, Turkey: Nezahat Gökyiğit Botanik Bahçesi ve Flora 10.1016/j.rser.2016.08.010 Araştırmaları Derneği. Colak AM, Kupe M, Bozhuyuk RM, Ercisli S, Gundogdu M (2019). Piovan A, Cassina G, Filippini R (2011). Crambe tataria: actions for Identification of some fruit characteristics in wild bilberry ex situ conservation. Biodiversity and Conservation 20: 359- (Vaccinium myrtillus L.) accessions from Eastern Anatolia. 371. doi: 10.1007/s10531-010-9949-z Gesunde Pflanzen 70:31-38. Prina AO (2009). Revisióntaxonómica del género Crambe sect. Comlekcioglu N, Karaman S, Ilcim A (2008). Oil composition Crambe (Brassicaceae, Brassiceae). Anales del Jardín Botánico and some morphological characters of Crambe orientalis de Madrid 66: 7-24. doi: 10.3989/ajbm.2186 var. orientalisand Crambe tataria var. tataria from Rudloff E, Wang Y (2011).Crambe . In: Kole C (editor). Wild Crop Turkey. Natural Product Research 22: 525-532. doi: Relatives: Genomic and Breeding Resources Oilseeds. Berlin, 10.1080/14786410701592349 Germany: Springer Verlag, pp. 97-116. doi: 10.1007/978-3- Dolya VS, Shkurupii EN, Podzolkova TV, Kaminskii NA (1973). The 642-14871-2 seed oils of some species of the family Cruciferae. Chemistry Saastamoinen M, Kumpulainen J, Nummela S (1989). Genetic of Natural Compounds 9 (1): 12-14.doi: 10.1007/BF00580878 and environmantalvariation in oil content and fatty acid Ersoy N, Kupe M, Gundogdu M, Gulce I, Ercisli S (2018). composition of oats. Cereal Chemistry 66: 296-300. Phytochemical and antioxidant diversity in fruits of currant (Ribes spp.) cultivars. Natulae Botanicae Horti Agrobotanici Sampaio GR, Saldanha T, Soares RAM, Torres EAFS (2012). Effect of Cluj-Napoca 46 (2): 381-387. natural antioxidant combinations on lipid oxidation in cooked chicken meat during refrigerated storage. Food Chemistry 135 Gastaldi G, Capretti G, Focher B, Cosentino C (1998). (3): 1383-1390. doi: 10.1016/j.foodchem.2012.05.103 Characterization and proprieties of cellulose isolated from the Crambe abyssinica hull. Industrial Crops and Products 8: 205- Tarıkahya-Hacıoğlu B (2016). Molecular diversity of the wild 218. doi: 10.1016/S0926-6690(98)00004-1 Crambe (Brassicaceae) taxa in Turkey detected by inter-simple sequence repeats (ISSRs). Industrial Crops and Products 80: Gecer MK, Kan T, Gundogdu M, Ercisli S, Ilhan G et al. (2020). 214-219. doi: 10.1016/j.indcrop.2015.11.065 Physicochemical characteristics of wild and cultivated apricots (Prunus armeniaca L.) from Aras valley in Turkey. Genetic Umarov AU (1975). The seed oils of the family Cruciferae. Chemistry Resources and Crop Evolution 67: 935-945. of Natural Compounds 11 (1): 10-12. Goffman FD, Thies W, Velasco L (1999). Chemotaxonomic value of Uyaroğlu A (2018). An experimental study on performance and tocopherols in Brassicaceae. Phytochemistry 50: 793-798. doi: emissions of a single cylinder direct injection diesel engine 10.1016/S0031-9422(98)00641-4 with Crambe abyssinica and Crambe orientalis biodiesels. International Journal of Automotive Engineering and Lalas S, Gortzi O, Athanasiadis V, Dourtoglou E, Dourtoglou V Technologies 7: 142-148. doi: 10.18245/ijaet.476197 (2012). Full characterisation of Crambe abyssinica Hochst. seed oil. Journal of the American Oil Chemists’ Society 89: 2253- Vollmann J, Ruckenbauer P (1993). Agronomic performance and oil 2258. doi: 10.1007/s11746-012-2122-y quality of crambe as affected by genotype and environment. Bodenkultur 44: 335-343. Lazzeri L, Leoni O, Conte LS, Palmieri S (1994). Some technological characteristics and potential uses of Crambe abyssinica Warwick SI, Black LD (1997). Phylogenetic implications of chloroplast products. Industrial Crops and Products 3: 103-112. doi: DNA restriction site variation in subtribes Raphaninae and 10.1016/0926-6690(94)90083-3 Cakilinae (Brassicaceae, tribe Brassiceae). Canadian Journal of Botany 75: 960-973. doi: 10.1139/b97-107 Matthäus B, Brühl L (2001). Comparison of different methods for the determination of the oil content in oilseeds. Journal of Warwick SI, Francis A, Gugel RK (2009). Guide to Wild Germplasm the American Oil Chemists’ Society 78: 95-102. doi: 10.1007/ of Brassica and Allied Crops (tribe Brassiceae, Brassicaceae). s11746-001-0226-y 3rd ed. Ottawa, ON, Canada: Agriculture and Agri-Food Canada (AAFC) . MikolajczakKL, Miwa TK, Earle FR, Wolff IA, Jones Q (1961). Search for new industrial oils. V. Oils of Cruciferae. Journal of Zia-Ul-Haq M, Ahmad S, Qayum M, Ercişli S (2013). Compositional the American Oil Chemists’ Society 38: 678-681. doi: 10.1007/ studies and antioxidant potential of Albizia lebbeck (L.) Benth. BF02633053 pods and seeds. Turkish Journal of Biology 37 (1): 25-32.

670